Monomeric emulsion stabilizers containing an n-diallylacetamido or n-dimethallylacetamido radical

ABSTRACT

Quaternary ammonium salts having an N-diallylacetamido or Ndimethallylacetamido radical and a lipophilic radical covalently linked to the quaternized nitrogen are disclosed. These quaternary ammonium salts are useful as monomeric emulsion stabilizers.

nited States atent [1 1 Samour et a1.

[ 51 Feb. 27, 1973 [54] MONOMERIC EMULSION STABILIZERS CONTAINING AN N-DIALLYLACETAMIDO OR N DIMETHALLYLACETAMIDO RADICAL [75] Inventors:Carlos M. Samour, Wellesley; Mildred C. Richards, Wakefield, both ofMass.

[73] Assignee: The Kendall Company, Walpole,

Mass.

[22] Filed: May 26,1970

[21] Appl. No.: 40,715

[56] References Cited UNITED STATES PATENTS 2,168,253 8/1939 Balle et a1..260/561 A 2,176,896 10/1939 Epstein et al. 2,411,662 11/1946 Martin etal. ....260/S61 A Primary ExaminerElbert L. Roberts AssistantExaminer-Ethel G. Love Att0rney-Ellen P. Trevors and Robert D. Chodera[57] ABSTRACT Quaternary ammonium salts having an N-diallylacetamido orN-dimethallylacetamido radical and a lipophilic radical covalentlylinked to the quatemized nitrogen are disclosed. These quaternaryammonium salts are useful as monomeric emulsion stabilizers.

11 Claims, No Drawings MONOMERIC EMULSION STABILIZERS CONTAINING ANN-DIALLYLACETAMIDO OR N- DIME'IIIALLYLACETAMIDO RADICAL This inventionrelates to stabilizing agents for emulsion polymerization. Moreparticularly it relates to a class of quatemized organic salts whichserve simultaneously as stabilizing agents for emulsion polymerizationsand as monomeric reactants in the polymerization, so that the saltsbecome an integral part of the polymer, which is thereby self-stabilizedwithout the use of surfactants.

Polymeric latices, derived from ethylenically-unsaturated monomers, areWidely used for a variety of applications, such as adhesive masses andbinders for nonwoven fabrics. Most conventional polymeric latices are 7produced by an emulsion polymerization process, in which monomericmaterials are polymerized while they are dispersed in an aqueous mediumby means of a surface active agent. The surface active agent may beanionic in nature, such as soap or sodium lauryl sulfate. Alternatively,it may be of a nonionic type as represented by various ethylene oxidederivatives, or by polyhydroxy compounds, or it may be cationic, asrepresented by alkyl ammonium halides. Cationic agents are preferablycombined with a nonionic agent for improved performance. Thepolymerization of monomeric materials is also frequently affected in thepresence of water-soluble protective colloids or stabilizing agents. Anyof the above emulsifying or stabilizing agent leads to the presence of awater-sensitive ingredientin the final polymeric latex. For latexutilizations wherein wet strength and resistance to the influence ofwater are desirable, as in. most paper coatings, nonwoven fabrics,certain pressure-sensitive adhesive tapes, and the like, the presence ofa watersensitive ingredient in the polymeric mass is undesirable.

A preferred method of avoiding the presence of water-sensitive elementsin a polymeric latex is to employ what is termed herein monomericemulsion stabilizers that is, a class of organic monomer whichcopolymerizes with the ethylenically unsaturated monomers, becoming apart of the final polymer, but which stabilizes the polymerizationprocess against the formation of coagulum and against subsequent phaseseparation. In accordance with this invention, it has been found thatselected quaternary ammonium salts wherein an N-diallylacetamido orN-dimethallylacetamido radical and a lipophilic radical are covalentlylinked to the quaternized nitrogen are excellent monomeric emulsionstabilizers for the polymerization of ethylenically unsaturatedmonomers.

More particularly, the compounds of this invention have the formulawherein R 1 is hydrogen or methyl; R, and R are independently selectedalkyl, hydroxyalky], aryl, R,,- COCH,- or R -NHCO -CI-l, wherein R, ishydrogen .or alkyl, or together part of a heterocyclic amino radical inwhich the quaternary nitrogen atom in preferably ethylene,

formula I is part of the ring; R, is a lipophilic radical; and X ishalide, alkyl sulfate, alkyl benzene sulfonate, phenoxy (or alkylphenoxy) alkylene (or polyalkyleneoxy) sulfate, dialkyl sulfosuccinateor alkyl phosphate.

These compounds I are readily prepared from available materials, andthus are attractive for use in commercial operations.

While any compound having the general formula I canbe provided accordingto this invention, preferred monomeric emulsion stabilizers includethose compounds I wherein R, is hydrogen or methyl;

R, and R are a. independently selected from the group consisting ofalkyl or hydroxyalkyl having one to seven carbon atoms, benzyl, R',-O-COCH,- and R NI-I-COCH,- where R, is hydrogen or alkyl having oneto four carbon atoms; or b. together part of a morpholinium orpiperidinium moiety;

R is a lipophilic radical; and

X" is halide, alkyl sulfate wherein the alkyl moiety has one to 18carbon atoms, alkyl benzene sulfonate wherein the alkyl group has one to12 carbon atoms, R"C,,H OCH,CHR"' O,, CI-b-CHR' SO; wherein R" ishydrogen or alkyl having one to 12 carbon atoms, R' is hydrogen ormethyl and n is zero or an integer, dialkyl sulfosuccinate wherein thealkyl group has one to 24 carbon atoms, or alkyl phosphate wherein thealkyl group has one to 18 carbon atoms.

By the term lipophilic radical in the claims and specification herein ismeant a radical containing an aliphatic hydrocarbon chain having fromabout seven to about 28 carbon atoms, and preferably from about nine toabout 18 carbon atoms, including saturated, unsaturated, straight-chainand branched groups. This aliphatic hydrocarbon chain can be covalentlylinked to the nitrogen either directly or through an intermediatelinkage as illustrated below where L represents the aliphatichydrocarbon chain:

a benzyl group,

an ester or amide group such as CI-I CHR'- ACO--L wherein R is hydrogenor methyl and A is oxygen or NH;

a polyalkylene oxide group such as CH,-CHR (o-CH CH 6)n- L wherein R ishydrogen or methyl and n is zero to 4; an acetoxy or acetamido groupsuch as -CH,COOL and CI-I,CO NHL; alkylene ethers such as -CI-I,-O--Land Cl-l,- CI'l,-OL; a hydroxysuccinyloxy or hydroxysuccinylamino grouphaving the formula R,--AC0 CHL-CH COOH wherein R is a diradical,

propylene, isopropylene, 2- hydroxypropylene, acetoxypropylene, or--CI-I CHR (OCH,CI-IR,,),,- where R; is hydrogen or methyl and n is zeroto-4, and A is oxygen or --NH;

and isomers of the aforementioned hydroxysuccinyloxy orhydroxysuccinylamino groups wherein the aliphatic hydrocarbon chain L isattached to the carbon atom adjacent to the carboxyl group.

The monomeric emulsion stabilizers having the formula I can besynthesized by several convenient methods. For example, all compounds Iwhere X is ha lide, except those where the lipophilic radical comprisesan intermediate hydroxysuccinyloxy or hydroxysuccinylamino linkage, canbe provided by reacting an N-diallyl-Z-haloacetamide or N-dimethallyl-2-haloacetamide with a tertiary amine having the formula R,R R wherein R Rand R are as previously described or with a mixture of tertiary aminesdiffering in the identity of the R group.

Illustrative tertiary amines suitable for use in the preparation ofcompounds I include methyl n-butyl heptyl amine; methyl dodecylaminoethanol; di-n-butyl dodecyl amine; di-nheptyl n-nonyl amine; methylbenzyl iso-octadecyl amine; dimethyl octacosyl amine;

N-(decanoyloxy ethyi)piperidine; dodecyl N- dimethylaminoacetate;hexadecyl N- dimethylaminoacetate; N-decyl N'- dimethylaminoacetamide;N-nonylbenzyl N diethylaminoacetamide; lauroyl (polyethyleneoxy) N-dimethylamine; decyloxyethyl N-dibutylamine; methylN-hexadecyl-N-methylaminoacetate, etc.

Compounds I, excluding those where R comprises an intermediatehydroxysuccinyloxy or hydroxysuccinylamino linkage, are also provided byreacting N-diallyl-2-haloacetamide or N-dimethallyl-2-ha1oacetamide witha secondary amine having the formula R,R NH or R R Nl'I to provide anintermediate tertiary amine which is subsequently quaternized with acompound such as ethyl chloroacetate, propyl chloroacetate,chloroacetamide, methyl bromide, dibutyl sulfate, dodecyl bromide,tridecyl chloroacetate, etc. It will be apparent that the aforementionedreactants will be selected so that there is at least one lipophilicradical in the resulting monomeric emulsion stabilizer I.

Compounds I wherein X- is halide and R, is a lipophilic radicalcomprising an aliphatic hydrocarbon chain covalently linked to thequaternary nitrogen through a hydroxysuccinyloxy or hydroxysuccinylaminolinkage can be readily prepared by reacting N-diallyl-Z-haloacetamide orN-dimethallyl-Z- haloacetamide with a tertiary amino alcohol or amine toprovide an intermediate which is subsequently reacted with a succinicanhydride having an aliphatic hydrocarbon group in accordance with thefollowing equations wherein R,, X, R,, R R,, A and L are as previouslydescribed.

nccm

Exemplificative tertiary-amino alcohols and amines II suitable for usein the preparation of compounds I inelude dimethylaminoethanol,methylpropylaminopropanol, dibutylamino isopropylamine,3-(N-dimethylamino)-2-acetoxypropanol-l and N- (hydroxypropyl)piperidine.

The succinic anhydrides having an aliphatic hydrocarbon group arereadily provided by known methods, such as by reacting maleic anhydridewith an olefin as described in US. Pat. No. 2,741,597. Illustrativecompounds include heptenyl succinic anhydride, octacosasuccinicanhydride, n-heptyl succinic anhydride, iso-octadecenyl succinicanhydride, etc.

Alternately, the above-described process can be reversed by firstreacting the tertiary-amino compound II with the succinic anhydridefollowed by reaction with N-diallyl-2-haloacetamide or N-dimethallyl-Z-haloacetamide. Mixtures of succinic anhydrides differing in the identifyof the aliphatic hydrocarbon group can also be employed.

Another procedure for the preparation of compounds I wherein R is alipophilic radical comprising an aliphatic hydrocarbon chain convalentlylinked to the quaternary nitrogen through a hydroxysuccinyloxy orhydroxysuccinylamino linkage comprises the reaction of a succinicanhydride having an aliphatic hydrocarbon group with an appropriatetertiary amino alcohol or amine containing a diallylacetamido ordimethallylacetamido radical, followed by quaternization as illustratedin the following equation. However, those compounds wherein R and R arepart of a morpholinium or piperidinium moiety cannot be prepared by thismethod. Any of the previously described quatemizing agents can be usedin this reaction.

lquatnrniziu agent Compounds I herein X is other than halide can beprovided by reacting the corresponding quaternary ammonium halide withan alkali metal or ammonium salt such as an alkali metal alkyl sulfate,an alkali metal alkyl benzene sulfonate, an ammonium alkyl phenoxypolyalkyleneoxy alkylene sulfate, an alkali metal dialkyl sulfosuccinateor an alkali metal alkyl phosphate. Exemplificative salts include sodiumlauryl sulfate, sodium oleoyl sulfate, sodium dodecyl benzene sulfonate,di-tridecyl sodium sulfosuccinate, di-octyl sodium sulfosuccinate,sodium octadecyl phosphate, sodium di-Z-ethylhexyl phosphate, etc.

The aforementioned reactions to provide the monomeric emulsionstabilizers l are generally carried out at temperatures from about 0 toC, but higher or lower temperatures can be employed.

Although the reactions proceed readily in the absence of a solvent,diluents such as water, acetonitrile, dimethylformamide, ethyl acetate,methanol and methylene chloride can be suitably employed. Monomers suchas acrylonitrile and ethyl acrylate can also be utilized as solvents inthe preparation of the monomeric emulsion stabilizers. While compounds Ican be isolated prior to use in polymerization reactions, preferablythey are used in their reaction solutions.

Particularly preferred monomeric emulsion'stabilizers include thosecompounds I wherein R is hydrogen; R and R are a. independently selectedalkyl having one to four carbon atoms, or b. together part of amorpholinium or piperidinium moiety; R is a lipophilic radicalcontaining an aliphatic hydrocarbon chain having about nine to about 18carbon atoms; and X" is chloride or bromide. 0f the aforementionedcompounds, those wherein R and R are methyl or ethyl, and preferablymethyl, are most suitable for commercial applications.

Illustrative ethylenically unsaturated monomers suitable forcopolymerizing with the monomeric emulsion stabilizers of this inventioncomprise vinyl acetate, vinyl chloride, acrylonitrile, and acrylicmonomers in general represented by the formula where R is a hydrogenatom or a methyl group, and R is an alkyl radical of one to 14, andpreferably one to four carbon atoms. As is known in the art of preparingacrylic ester polymers, the softness of the polymer and the difficultyof initiating polymerization increase as the number of carbon atoms inthe ester group increases. In the practice of this invention, when theacrylic monomer contains more than 8 carbon atoms in the ester group, itis advantageous for ease of initiation and polymerization to mixtherewith at least about 20 mole percent of an acrylic ester with fewerthan four carbon atoms in the ester group.

Mixtures of more than one such ethylenically unsaturated monomer may beused, and in order to impart special properties of toughness, rigidity,or cross-linking reactivity to the polymer, a minor proportion, usuallyless than 20 mole percent, of the major monomer may be replaced by someother ethylenically unsaturated monomer such as vinyl esters other thanvinyl acetate as typified by vinyl laurate and vinyl stearate; vinylethers such as vinyl methyl ether, vinyl ethyl ether, and vinyl butylether; di-unsaturated monomers such as diethylene glycol diacrylate,ethylene glycol diitaconate, diallyl phthalate, divinyl benzene and thelike; acrylic and methacrylic acids, acrylamide and methacrylamide,hydroxyethyl acrylate and methacrylate, hydroxypropyl acrylate andmethacrylate, and styrene.

In general, in the polymerization process of this invention, 0.1 to 10percent by weight of monomeric emulsion stabilizer is employed, with lto 5 percent by weight being preferred. The amount of monomeric emulsionstabilizer is based on the totalmonomers added to the polymerizationreaction.

cording to this invention in which the solid polymer content is 40 to 50percent by weight. If desired, the solids content may be diluted to 1percent by weight or less, with excellent retention of stability at boththe higher and lower concentrations.

The monomeric emulsion stabilizers of this invention are useful in bothbatch and continuous polymerization processes.

The following examples will serve to illustrate the practice of thisinvention.

EXAMPLE 1 A mixture of N-diallyl-2-chloroacetamide (18.6 g.) anddimethyl dodecyl amine (22.5 g.) in 139 g. of water was tumbled for 24hours at room temperature to provide a clear, homogeneous solution. Thissolution was allowed to stand at room temperature for 48 hours. Chlorideion analysis confirmed that diallylacetamido dimethyl dodecyl ammoniumchloride had been obtained.

EXAMPLE 2 A mixture of N-diallyl-2-chloroacetamide (18.6 g.) anddimethyl hexadecyl amine (27.8 g.) in 46.4 g. of acetonitrile wasallowed to stand for four days at room temperature. Chloride ionanalysis confirmed that diallylacetamido dimethyl hexadecyl ammoniumchloride had been obtained. The solvent was removed under vacuum,thereby providing a yellow, waxy solid.

A 25 percent by weight aqueous solution of this compound was prepared.The amount of 9 g. of the aqueous solution was charged to a four-neckresin kettle equipped with a thermometer, stirrer, nitrogen inlet anddropping apparatus and ethyl acrylate g.) and water (280 g.) added. ThepH of the resulting emulsion was about 5.0. After cooling to 16 C by theuse of an ice bath, 10 ml of 3 percent H 0, in H 0 were added to theemulsion followed by dropwise addition of a reductant solutioncomprising 0.02 g. ferrous ammonium sulfate and 0.4 g. ascorbic acid in10 ml H O. Polymerization was initiated after 0.8 ml of reductantsolution had been added as evidenced by an exotherm of about 22 in 5minutes. A total of 3 ml of reductant solution was added untilcompletion of the polymerization as evidenced by a lack of exotherm uponthe further addition of a slight amount of I-I,,,O and reductant. Theyield of polymer was percent of theoretical, and no coagulum formed.

EXAMPLE 3 Following the general procedure of Example 2, a mixture ofdimethyl (2-lauroyloxyethyl) amine (13.6 g.) andN-diallyl-2-chloroacetamide (9.3 g.) in 22.9 g. of dimethylformamide wasallowed to stand for 16 days at room temperature. A clear homogeneoussolution was obtained. Ether was added to the solution therebyprecipitating a white crystalline material which was isolated from thereaction solution. Chloride ion analysis confirmed that diallylacetamidodimethyl lauroyloxyethyl ammonium chloride had been obtained.

The amount of 2.4 g. of this compound was dissolved in 240 g. of H 0 and55 g. of ethyl acrylate and 25 g. of butyl acrylate added; the pH of theresulting emulsion was about 5. After cooling to 19 C, polymerizationwas initiated and maintained by the addition of 10 m1 of 3 percent 11 0,in H followed by the dropwise addition of the reductant solutiondescribed in Example 2. A total of 4 ml of reductant solution and anadditional 2 ml of 11,0, solution was employed in the polymerization.The yield of polymer was 95 percent of theoretical and no coagulumformed.

EXAMPLE 4 A mixture of N-diallyl-2-chloroacetamide (18.6 g.) anddimethyl amino ethanol (8.9 g.) in 27.5 g. of acetonitrile was allowedto stand at room temperature for 24 hours. A clear, homogeneous solutioncontaining 98 percent of the theoretical chloride was obtained. Theamount of 26.6 g. of tetrapropenyl succinic anhydride, which is analkenyl succinic anhydride having an average of 12 carbon atoms and onecarbon-carbon double bond, was added to the solution; the reaction wasslightly exothermic. After allowing the reaction solution to stand for24 hours at room temperature, the solvent was removed under vacuum toprovide 47 g. of viscous, yellow liquid product. Analysis for carboxylion content confirmed that diallylacetamido dimethyltetrapropenylhydroxysuccinyloxyethyl ammonium chloride had beenobtained.

An emulsion was prepared from ethyl acrylate (280 g.), butyl acrylate(35 g.), acrylonitrile (35 g.) and 11,0 (1,000 g.) employing 10.5 g. ofthe above monomeric emulsion stabilizer. The pH of the resultingemulsion was 4.5. After cooling to 13C, polymerization was carried outemploying 35 ml of 3% 11,0 in 11,0 followed by the dropwise addition of10.5 ml of the reductant solution described in Example 2. The yield ofpolymer was 92 percent of theoretical.

EXAMPLE 5 N-diallyl-2-chloroacetamide (6.6 g.) andN-lauroylaminopropyl-N'-dimethy1amine (10.0 g.) were dissolved in amixture of acetonitrile (16.6 g.) and dimethylformamide (16.6 g.). Thereaction solution was allowed to stand at room temperature for 24 hours.Filtration provided a while solid which was washed with ether and driedat room temperature under vacuum. Chloride ion analysis confirmed thatdiallylacetamido dimethyl lauroylaminopropyl ammonium chloride had beenobtained.

To the amount of 2.25 g. of the above compound in 250 g. of H 0 wasadded 75 g. of ethyl acrylate; the pH of the resulting emulsion was4.5-5.0. After cooling to 12 C, polymerization was carried out employingml of 3% 11,0, in H 0 and 3 ml of the reductant solution described inExample 2. The conversion to polymer was 95 percent of theoretical andno coagulum formed.

EXAMPLE 6 The amount of 1.3 g. of the diallylacetamido dimethyllauroylaminopropyl ammonium chloride prepared in Example 5 was reactedwith 1.0 g. of sodium dodecyl benzene sulfonate in 240 g. of water toprovide diallylaminocarbonylmethyl dimethyl lauroylaminopropyl ammoniumdodecyl benzene sulfonate.

EXAMPLE 7 N-diallyl-Z-chloroacetamide (18.6 g.) was added to'y-dimethylarninopropyl amine (10.2 g.) in 28.8 g. acetonitrile; ahighly exothermic reaction resulted. After allowing the reactionsolution to stand for 48 hours at room temperature, 100 percent of thetheoretical chloride ion content was determined by titration.Tetrapropenyl succinic anhydride (26.6 g.) was added to the reactionsolution. Removal of solvent under vacuum provided an extremely viscousredbrown liquid. Carboxyl ion analysis confirmed that diallylacetamidodimethyl tetrapropenylhydroxysuccinylamidopropyl. ammonium chloride hadbeen ob tained.

A mixture of ethyl acrylate (280 g.), butyl acrylate (35 acrylonitrile(35 g.) and H 0 (1,000 g.) was emulsified using 21 g. of the abovemonomeric emulsion stabilizer. The pH of the resulting emulsion was 4.5.After cooling to 14 C, polymerization was carried out employing 35 ml of3% H O, in H O followed by the dropwise addition of 13 ml of thereductant solution of Example 2. No coagulum formed and the conversionpolymer was 94 percent of theoretical.

EXAMPLE 8 N-diallyl-2-chloroacetamide (18.6 g.) and 27.4 g. ofN-cocomorpholine, which is a mixture of substituted morpholinescomprising about 53.0 percent lauryl amine, 19.0 percent myristyl amine,with the balance being predominately a mixture of morpholines havingother saturated hydrocarbon substituents, were mixed at room temperaturein 40.0 g. acetonitrile. The reaction was refluxed for 5 hours. Chlorideion analysis confirmed that diallylacetamido N-cocomorpholinium chloridehad been obtained. Removal of solvent under vacuum provided a partiallycrystalline product.

Ethyl acrylate g.) in 240 g. of B 0 was emulsified using 2.4 g. of theabove monomeric emulsion stabilizer. The pH of the resulting emulsionwas 4.56.0. After cooling to 15 C, polymerization was carried outemploying 12 ml of 3% H O, in [-1 0 and 6 ml of the reductant solutiondescribed in Example 2. The conversion to polymer was 87 percent oftheoretical.

What is claimed is:

l. A compound having the formula wherein R is hydrogen or methyl, R, andR are independently selected alkyl or hydroxyalkyl having one to sevencarbon atoms, R, is a lipophilic radical containing an aliphatichydrocarbon chain having from about seven to about 28 carbon atoms, andX" is halide or alkyl benzene sulfonate wherein the alkyl group has oneto 12 carbon atoms.

2. The compound of claim ll wherein R is hydrogen or methyl, R, and Rare independently selected alkyl or hydroxyalkyl having one to 7 carbonatoms, R is a lipophilic radical containing an aliphatic hydrocarbonchain having from about seven to about 28 carbon atoms, and X is halide.

3. The compound of claim 2 wherein R, is hydrogen; R and R areindependently selected alkyl having one to four carbon atoms; R is alipophilic radical containing an aliphatic hydrocarbon chain havingabout nine to about 18 carbon atoms; and X is chloride or bromide.

4. The compound of claim 3 having the formula wherein X is chloride orbromide, R is hydrogen or methyl, A is oxygen or nitrogen and L is analiphatic hydrocarbon group having from about nine to about 18 carbonatoms.

8. The compound of claim I having the name diallylacetamido dimethyllauroyloxyethyl ammonium chloride.

9. The compound of claim 7 having the name diallylacetamido dimethyllauroylaminopropyl ammonium chloride.

10. The compound of claim 1 wherein R is hydrogen; R, and R areindependently selected alkyl having 1 to 4 carbon atoms; R is alipophilic radical containing an aliphatic hydrocarbon chain havingabout nine to about 18 carbon atoms; and X is an alkyl benzene sulfonateradical wherein the alkyl group has from about one to about 12 carbonatoms.

1 1. The compound of claim 10 having the name diallylacetamido dimethyllauroylaminopropyl ammonium dodecylbenzenesulfonate.

2. The compound of claim 1 wherein R1 is hydrogen or methyl, R2 and R3are independently selected alkyl or hydroxyalkyl having one to 7 carbonatoms, R4 is a lipophilic radical containing an aliphatic hydrocarbonchain having from about seven to about 28 carbon atoms, and X is halide.3. The compound of claim 2 wherein R1 is hydrogen; R2 and R3 areindependently selected alkyl having one to four carbon atoms; R4 is alipophilic radical containing an aliphatic hydrocarbon chain havingabout nine to about 18 carbon atoms; and X is chloride or bromide. 4.The compound of claim 3 having the formula
 5. The compound of claim 4having the name diallylacetamido dimethyl dodecyl ammonium chloride. 6.The compound of claim 4 having the name diallylacetamido dimethylhexadecyl ammonium chloride.
 7. The compound of claim 3 having theformula
 8. The compound of claim 7 having the name diallylacetamidodimethyl lauroyloxyethyl ammonium chloride.
 9. The compound of claim 7having the name diallylacetamido dimethyl lauroylaminopropyl ammoniumchloride.
 10. The compound of claim 1 wherein R1 is hydrogen; R2 and R3are independently selected alkyl having 1 to 4 carbon atoms; R4 is alipophilic radical containing an aliphatic hydrocarbon chain havingabout nine to about 18 carbon atoms; and X is an alkyl benzene sulfonateradical wherein the alkyl group has from about one to about 12 carbonatoms.
 11. The compound of claim 10 having the name diallylacetamidodimethyl lauroylaminopropyl ammonium dodecylbenzenesulfonate.